t-Bu-QuinoxP* ligand: Applications in asymmetric pd-catalyzed allylic substitution and Ru-catalyzed hydrogenation

被引:49
作者
Imamoto, Tsuneo [1 ]
Nishimura, Miwako [1 ]
Koide, Aya [1 ]
Yoshida, Kazuhiro [1 ]
机构
[1] Chiba Univ, Grad Sch Sci, Dept Chem, Inage Ku, Chiba 2638522, Japan
关键词
HIGHLY ENANTIOSELECTIVE HYDROGENATION; OXAZOLINE LIGANDS; MONODENTATE; COMPLEXES; PHOSPHORAMIDITES; ALKYLATIONS;
D O I
10.1021/jo071192k
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] The potential of the t-Bu-QuinoxP* ligand (1) as a chiral ligand in asymmetric synthesis was examined. The ligand exhibited good to excellent asymmetric induction in Pd-catalyzed asymmetric allylic substitution of 1,3-diphenyl-2propenyl acetate (up to 98.7% ee) and in Ru-catalyzed asymmetric hydrogenation of ketones (up to 99.9% ee).
引用
收藏
页码:7413 / 7416
页数:4
相关论文
共 38 条
[1]   Highly rigid diphosphane ligands with a large dihedral angle based on a chiral spirobifluorene backbone [J].
Cheng, X ;
Zhang, Q ;
Xie, JH ;
Wang, LX ;
Zhou, QL .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (07) :1118-1121
[2]   New P-chirogenic phosphine ligands and their use in catalytic asymmetric reactions [J].
Crépy, KVL ;
Imamoto, T .
NEW ASPECTS IN PHOSPHORUS CHEMISTRY III, 2003, 229 :1-40
[3]   Synthesis of monodentate chiral spiro phosphonites and the electronic effect of ligand in asymmetric hydrogenation [J].
Fu, Y ;
Hou, GH ;
Xie, JH ;
Xing, L ;
Wang, LX ;
Zhou, QL .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (23) :8157-8160
[4]  
Gridnev ID, 2001, ADV SYNTH CATAL, V343, P118, DOI 10.1002/1615-4169(20010129)343:1<118::AID-ADSC118>3.3.CO
[5]  
2-Q
[6]   The development of bidentate P,N ligands for asymmetric catalysis [J].
Guiry, PJ ;
Saunders, CP .
ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (05) :497-537
[7]   Highly selective asymmetric hydrogenation using a three hindered quadrant bisphosphine rhodium catalyst [J].
Hoge, G ;
Wu, HP ;
Kissel, WS ;
Pflum, DA ;
Greene, DJ ;
Bao, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (19) :5966-5967
[8]  
Hu AG, 2002, ANGEW CHEM INT EDIT, V41, P2348, DOI 10.1002/1521-3773(20020703)41:13<2348::AID-ANIE2348>3.0.CO
[9]  
2-K
[10]   Unsymmetrical hybrid ferrocene-based phosphine-phosphoramidites: A new class of practical Ligands for Rh-catalyzed asymmetric hydrogenation [J].
Hu, XP ;
Zheng, Z .
ORGANIC LETTERS, 2004, 6 (20) :3585-3588